


Why does Heaven care if Harry meets Sally?

by Casey Kelly (Over_autumns_ending)



Category: Supernatural
Genre: Destiel - Freeform, M/M
Language: English
Status: In-Progress
Published: 2012-11-10
Updated: 2012-11-23
Packaged: 2017-11-18 08:36:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,430
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/558994
Author URL: https://archiveofourown.org/users/Over_autumns_ending/pseuds/Casey%20Kelly
Summary: <blockquote class="userstuff">
              <p>Cupid decides to help Destiel come to fruition. Just remember, he isn't incontinent.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> “Love looks not with the eyes, but with the mind,  
> And therefore is winged Cupid painted blind.”  
> ― William Shakespeare, A Midsummer Night's Dream

_Stop hitting on him. He’s not interested in you, can’t you see that? Stop touching him. Don’t put your hand there!_

Dean’s inner monologue resembled a jealous partner as he watched the waitress with curly black hair fling herself at Castiel while he and Sam sipped their beers with strained expressions.

“You all right there, big guy?” Sam chuckled, patting his brother on the back.

“What?” Dean snapped to attention. “Yeah, of course. Why?”

“You just look ready to Molotov anyone that looks at you funny,” Sam said, giving him a look out the corner of his eye.

“Well, this is just annoying.” Dean waved his hand passively at the brunette who he was pretty sure was licking Castiel’s ear now. It further annoyed him to the usual look of pure terror on his best friend’s face. The pizza guy hadn’t taught him about ear licking.  
“We can’t even have a couple of beers in peace!” Dean said loud enough for the girl to hear. She turned and gave him a stink eye. Dean only smiled smugly as she hitched her leg off of Cas and sauntered away. “Now that’s better!” Dean smiled, drumming his fingers on the sticky table. His little brother only gave him a knowing smile out of his line of sight.

“Yes. It was quite vulgar, the things she was whispered to me. I didn’t not think your human bodies were able to do the things she was suggesting…” Cas said, shifting on his stool. “But it’s rather unusual for you to be so off put by female attention, Dean. Are you unwell?”

“What is the big fucking deal? I just wanted a boy’s night, alright?” Dean said, taking a hard swig of his beer and avoiding eye contact. “So sue me,” he added under his breath.

Sam and Cas exchanged looks that both seemed to say, “pissy much?”

“Boy’s night?” Sam laughed, putting the back of his hand to Dean’s forehead. “You feelin’ alright there, sunshine?” Dean angrily cut his eyes to his kin who was acting every bit the little brother at the moment. 

Cas took notice of Dean going out of his way to not make eye contact with him. He cocked his head to the side in that confused puppy way angels seemed to do. This caused Dean to glance in his direction, out of the corner of his eye, cheeks flushed, then quickly focused his green eyes somewhere else. Cas did love those eyes. He’d never seen eyes like the elder Winchester’s. Whenever he caught himself staring at either brother, he always thought God had taken special care in making the brothers, the entire Winchester clan actually. He knew if he said so out loud Dean would scoff and say that was “cheesy.” Cas still wasn’t sure what that expression meant. How could words correlate with a dairy product?

“Cas…” Dean’s voice pulled him out of his trance. “You’re staring again.”

“Sorry,” Cas said in his equally gravelly voice, dipping his head down in mock shame. He wasn’t actually ashamed, a little embarrassed for being caught, but not ashamed. He knew many humans that felt romantically about others of their same gender were made to feel less than human and worthy of his home. It always ruffled his feathers—literally—when he thought of people using his father’s name as a reason to hate and be vile to other human beings. As much as he disliked his father, he knew he would never punish someone for loving another person, regardless of gender. It was just preposterous.

“Christ, forget it!” Dean snapped, getting up and slipping his jacket on. “Let’s just get on the road already. We leave now we can get to New Mexico by sunrise. Get a head start on the case.”

The boys left Trudy’s Booze N’ Bar—Dean’s pick—but not before the brunette slipped a scrap of paper with her phone number on it to Cas with a slap on his ass and a flip of her finger to Dean when he turned around as goodbye.

“Charming,” Dean grumbled, pulling his keys out of his pocket. Cas was sure the brothers were focused on talking before he dropped the piece of paper and sliding into the Impala. The younger Winchester kept quiet as he slid in after the angel.

Before the boys got too far out of town Dean stopped to gas up while Sam went into the convenience store to get snacks. Dean hoped for nothing in the realm of healthy, but knew it was false hope. The pump stations weren't well lit so he couldn't see Castiel's face from the rear view mirror. He drummed his hands on the steering wheel and flicked knobs on the stereo.

"I've left an awkward silence again, haven't I?" He heard from the back seat.

Dean chuckled. "Yeah, we'll work on that one, buddy. Sorry I was so pissy back at the bar. Just tired, I guess."

"Tired..." Cas said doubtfully.

"Tired," Dean repeated, clearing his throat.

"I am someone you know quite well. You would say we are close...friends?" Cas asked. Dean thought he could hear the angel's voice shake, which made his shake.

"Of course, man. You're...you're my best friend, Cas," Dean said. It wasn't like him to come out with things like that. He wasn't sure why he did. He knew his feelings for Cas had sped past platonic months ago, but he couldn't bring himself to come to terms with it. He was Dean fucking Winchester. He slept with women, he fell for women. But he knew deep down that wasn't him anymore, even when he was in love with Lisa, it never reached the point it had with Cas, but those feelings were staying deep down in his depths.

"Dean, I--" Before Cas could finish Sam opened up the passenger door of the Impala and noisy plopped down into the seat with two plastic bags of snacks. He looked at his brother and their adoptive angel.

"Well...I definitely interrupted something," he said.

"Just close the door, Sammy," Dean sighed. He turned Bon Jovi back up and drummed along until they hit the New Mexico border.

When they made it to a motel in Roswell, Sam and Cas went to park the Impala while Dean got them a room. Sam turned off the engine but left the keys in the ignition and leaned over the steering wheel with a big sigh.

"I saw you throw away that girl's phone number," he said almost inaudibly. He knew Cas heard him though.

"I was not interested in the girl," Cas said in his matter-of-fact tone.

"Pretty girl though..." Sam turned around to lock eyes with the angel. "You care about Dean."

"Sam," Cas groaned, rollings his eyes very robotically. Sam would have laughed at the human motion that he no doubt learned from Dean if he wasn't trying to have a serious conversation. "It is well known that I care for the Winchester brothers, Dean particularly."

"You know what I mean. You are interested in my brother in a way you weren't interested in that girl at the bar," Sam explained. Cas shifted uncomfortably, wrapping his trench coat tighter around himself. "Which I'm totally cool with!" Sam hurriedly added. "Nothing to be ashamed of. I actually think the two of you should put it out in the open and get rid of some of this sexual frustration."

"I'm not frust…"p>

Sam put his hand up. "Another expression, Cas."

"I don't believe your brother feels the same way as I do," Cas answered softly just as Dean opened the driver's side door.

"Come on, ladies," Dean said, tapping the top of the car before walking off in the direction of their room. Sam put his arm in front of Cas when they got out of the Impala to keep him back from Dean as they walked.

"He may not be the same Dean from ten years ago, but I still know my brother a bit," Sam said in a hushed tone. "Just...have a talk with him at some point. I'll be there if you want to kind of keep things relaxed. I think you'd be surprised by his reaction." Cas looked at him hard, the slightest bit of hope in his eyes and walked ahead.

 

Late, when bellies were full and eyelids were getting droopy, Dean announced he was getting a shower before Sam took all the hot water with his girly hour long ones. This garnered a tired bitch-face from him brother.

“Um…Dean. Can I speak to you a moment please?” Castiel said, voice faltering a bit on the last word.

Dean looked suspiciously at Cas and his brother. “And be willingly ambushed? I’ll pass.” He started walking towards the bathroom. Cas cowered in on himself a little more where he sat on the edge of one of the beds.

“Dean. This is serious,” Sam spoke up. “Sit down and shut up.” Dean looked at him like he was about to tell him where to shove it but he snapped his mouth closed and sat at the small table across from Cas. The angel looked as nervous as he had that time Dean took him to the strip club and suddenly Dean was just as nervous. Cas wouldn’t even look him in the eye. Dean pulled his chair closer, bumping knees with him.

“Cas, buddy. What’s wrong?” he asked, folding his arms and leaning forward.

“I…” Cas looked to Sam who gave a tender, encouraging smile. “Dean.”

“Cas.” Dean answered flatly.

“Dean…It is known that I care for the Winchesters a great deal.” Cas took a deep breath and kept his gaze focused on his and Dean’s shoes. Dean’s were perpetually muddy and scuffed while Cas’ were only slightly dull but rather clean. He wouldn’t mind buying Dean knew shoes. He deserved something nice and new after everything they’d been through, even if it were only shoes. “It’s also been discussed how I favor you and…Well it would seem I have developed feelings of a romantic nature towards you and—”

“Woah. Right there—stop!” Dean shot up from his seat and stepped back, almost slamming into the wall.

“Dean, let him finish. This is important,” Sam said, patting Cas on the back—who still hadn’t looked up from his now lonely shoes.

“Sammy, shut up!”

“Of course it’s not really your body that is the object of my attraction to you. It’s your soul. I am asexual as your kind likes to label so your body is really of no importance to me—of course it is a nice body. My father took great care in designing your body. Your soul is where my affection lies though.”

It was all said in one breath and Dean wasn’t even sure he’d caught everything said. He ran a hand over his face and sighed heavily. “I’m going to get a shower and pretend you didn’t say—” The flap of wings cut him off and he looked up to see Sam alone on the bed.

Sam looked from the empty spot next to him up to his brother. “Well should we just change your last name to Roman now?” Bitchface followed.

“Fuck you. You encouraged him,” was all Dean said before slamming the bathroom door behind him.


	2. Chapter 2

**Notes for the Chapter:**

> I promise you a longer chapter on the next update. I've just been ridiculously busy with work leading up to today. I real hope you like the story so far!

_Next morning; 6am._  
Dean was pulled out of fitful sleep by Sam vigorously shaking his shoulder and repeating his name like a chant.  
“What?!” Dean growled, angrily shedding the bed sheet from his legs and sitting up.  
“Cas never came back last night,” Sam said, looking around the motel room.  
Despite the still present anger at Cas from the previous night, alarm quickly set into his chest. “You sure?” he asked in a gruff morning voice, going into hunter mode. Sam nodded, getting up from the bed with Dean. The older brother stuffed his feet in his boots and slid his jacket over his shoulders before grabbing the keys to the Impala and motioning for Sam to follow.  
Once in the car and driving in what Dean hoped was the right direction, he called the cell phone he’d given Cas in case of emergencies.  
“Cas, dammit. Where the fuck are you?” he growled into his phone. “Cas, pick up your damn phone. I put minutes on it two days ago. Castiel!” He slapped the phone shut as it beeped signaling he reached the limit on his voice message.  
“You think he’d come if you pray?” Sa, asked, sliding his thumb across the screen of his phone.  
“Worth a shot.” Dean took a deep, slow breath. “Cas, who art a pain in my ass…get your feathery one in this car right now!” He gave it a minute and looked in his rearview mirror at the empty back seat. “Dammit!” He slammed his hand on the steering wheel and picked up his phone to call Castiel one more time.

 

“This will get him to admit his emotions, Castiel! Don’t worry, cousin!” The over-sized baby in a diaper clapped, dancing around Castiel who was strapped to a chair sitting on an angel sigil. “Oh look he’s calling again! He loves you so much. He just needs a push to admit it!”  
The giant baby picked Castiel’s phone from his coat pocket and flipped it open.  
“Hello, Dean!”  
There was a long pause on the other end.  
"…Cupid?!" Dean said from the other end of the phone line. "Where's Cas? Why are you answering his phone?"  
"Oh don't worry! I have him here with me. I found him wandering aimlessly last night. He was very upset, Dean. You really shouldn't lie to people about your feelings for them. It's okay to be a little different," Cupid said happily.  
"You son of a bitch! Where are you?" Dean demanded.  
"Yes, perfect! I'll tell you where we are and you can come confess your love and I'll let him go!" Cas stared at the fat angel wide-eyed. "Okay so we're -"  
"No! You can't!" Cas yelled. "Cupid. You can't do that to him."  
"Cas?!" he heard Dean yell from his phone.  
"Shut up, Castiel. You always were to serious. Let me do my job and have some fun while I'm at it." Cupid turned his attention back to the phone. "Okay, you will go eight miles out of Roswell. There's an old bomb shelter about ten minutes off the highway. We're in the basement. See you soon!"  
Dean ended the call and pressed the gas harder. "Fucking Cupid…What a dick!"


End file.
